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2-Thiopheneglyoxylic acid

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2-Thiopheneglyoxylic acid Basic information
Product Name:2-Thiopheneglyoxylic acid
Synonyms:Oxo(thien-2-yl)acetic acid 96%;2-oxo-2-thiophen-2-ylacetate;ALPHA-OXO-2-THIOPHENEACETIC ACID;2-THIENYLGLYOXYLIC ACID;2-THIOPHENEGLYOXYLIC ACID;2-OXO-2-(2-THIENYL)ACETIC ACID;alpha-oxothiophen-2-acetic acid;α-oxo-2-thiopheneacetic acid
CAS:4075-59-6
MF:C6H4O3S
MW:156.16
EINECS:223-794-2
Product Categories:Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes;Sulphur Derivatives;Thiophene&Benzothiophene;Organic acids;Heterocyclic Compounds
Mol File:4075-59-6.mol
2-Thiopheneglyoxylic acid Structure
2-Thiopheneglyoxylic acid Chemical Properties
Melting point 88-91 °C (lit.)
Boiling point 250.38°C (rough estimate)
density 1.404 (estimate)
refractive index 1.5151 (estimate)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
form solid
pka2.09±0.54(Predicted)
Sensitive Hygroscopic
BRN 115791
InChI1S/C6H4O3S/c7-5(6(8)9)4-2-1-3-10-4/h1-3H,(H,8,9)
InChIKeyGIWRVUADKUVEGU-UHFFFAOYSA-N
SMILESOC(=O)C(=O)c1cccs1
CAS DataBase Reference4075-59-6(CAS DataBase Reference)
Safety Information
Hazard Codes C,Xi
Risk Statements 34
Safety Statements 26-27-28-36/37/39-45
RIDADR UN 3261 8/PG 2
WGK Germany 3
Hazard Note Irritant
HazardClass 8
PackingGroup III
HS Code 29349990
Storage Class8A - Combustible corrosive hazardous materials
Hazard ClassificationsEye Dam. 1
Skin Corr. 1B
MSDS Information
ProviderLanguage
2-Thiopheneglyoxylic acid English
ACROS English
SigmaAldrich English
ALFA English
2-Thiopheneglyoxylic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
Uses2-Thiopheneglyoxylic acid was used in the synthesis of europium complexes.
Synthesis
ETHYL THIOPHENE-2-GLYOXYLATE

4075-58-5

2-Thiopheneglyoxylic acid

4075-59-6

The general procedure for the synthesis of 2-thiophene glyoxalate from ethyl thiophene-2-glyoxalate was as follows: to a solution of ethyl thiophene-2-glyoxalate (4 mL, 27.17 mmol) in ethanol (60 mL) was added an aqueous 4N sodium hydroxide solution (10.2 mL, 40.76 mmol). The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the reaction solution was acidified with 2N aqueous hydrochloric acid to pH 2. Subsequently, the solvent was removed by vacuum distillation to afford 2-thiophene glyoxalic acid as a yellow solid product (quantitative yield). The resulting residue was used directly in the subsequent reaction without further purification.LCMS analysis (Method 2): [MH-] = 155 with a retention time of 0.71 min.

References[1] Patent: WO2016/193244, 2016, A1. Location in patent: Page/Page column 80
[2] Chemical Communications, 2014, vol. 50, # 34, p. 4489 - 4491
[3] Patent: WO2016/177849, 2016, A1. Location in patent: Page/Page column 60
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4184 - 4190
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